IP Library Granted Patent US 10,077,233
Granted Patent B2
US 10,077,233 · App. 15/645,721 · Granted Sep 18, 2018

Poly-cyanostilbene macrocycles

Inventors: Amar H. Flood (Bloomington, IN); Semin Lee (Bloomington, IN); Kevin McDonald (Oak Park, IL)
Assignee: INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION
C07C255/47C07D213/57C07D249/06C07F7/1852C07C2603/90
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Quick Facts
Patent No.
US 10,077,233
App. No.
15/645,721
Granted
Sep 18, 2018
Kind
B2
Abstract

The present disclosure concerns synthesis and anion binding features of poly-cyanostilbene macrocycles of Formula (I):

Claims (16)

1. A complex comprising:

(a) an anion and

(b) a poly-cyanostilbene macrocycle of Formula (I):

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR 6 , —N(R 7 R 8 ), —CO 2 R 9 , —C(O)—N(R 10 R 11 ), wherein R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen,

wherein the anion is selected from BF 4 − , ClO 4 −, PF 6 − , N(SO 2 CF 3 ) 2 − , N(SO 2 C 2 F 5 ) 2 − , CH 3 SO 3 − , CF 3 SO 3 − , AsO 4 3− , AsF 6 − , AlCl 4 − , PO 4 3− , HPO 4 2− , H 2 PO 4 − , SO 4 2− , HSO 4 − , B(CN) 4 − , Cl − , Br − , I − , cyanide, BrO 4 − , IO 4 − , F − , HF 2 − , TcO 4 − , RPO 4 2− R 2 PO 4 − , RSO 3 − , SCN − , N 3 − , I 3 − , CO 3 2− HCO 3 − , FeCl 4 − , PtCl 6 2− , S n x− where n=1-8, and x=1 or 2, P 2 O 7 4− , HP 2 O 7 3− , H 2 P 2 O 7 2− H 3 P 2 O 7 − , a polyphosphate polyanion, a tetrazine anion, a dithiadiazolide anion, RBF 3 − , Ar—O − , wherein R comprises a substituent.

2. The complex of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 comprise identical substituents.

3. The complex of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 comprise tert-butyl groups.

4. The complex of claim 1 , wherein the poly-cyanostilbene macrocycle having Formula (I) is selected from the following:

5. A complex comprising:

(a) an anion and

(b) a poly-cyanostilbene macrocycle of Formula (IV):

wherein R 2 , R 3 , R 4 , and R 5 are selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR 6 , —N(R 7 R 8 ), —CO 2 R 9 , —C(O)—N(R 10 R 11 ), wherein R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen, and L comprising an alkyl moiety ranging from C 1-30 , said alkyl moiety comprising a saturated or unsaturated alkyl moiety, and optionally comprises substituents,

wherein the anion is selected from BF 4 − , ClO 4 − , PF 6 − , N(SO 2 CF 3 ) 2 − , N(SO 2 C 2 F 5 ) 2 − , CH 3 SO 3 − , CF 3 SO 3 31 , AsO 4 3− , AsF 6 − , AlCl 4 − , PO 4 3− , HPO 4 2− , H 2 PO 4 − , SO 4 2− , HSO 3 − , B(CN) 4 − , Cl − , Br − , I − , cyanide, BrO 4 31 , IO 4 − , F − , HF 2 − , TcO 4 − , RPO 4 2− , R 2 PO 4 − , RSO 3 − , SCN − , N 3 − , I 3 − , CO 3 2− , HCO 3 − , FeCl 4 − , PtCl 6 2− , S n x− where n=1-8, and x=1 or 2, P 2 O 7 4− , HP 2 O 7 3− , H 2 P 2 O 7 2− , H 3 P 2 O 7 − , a polyphosphate polyanion, a tetrazine anion, a dithiadiazolide anion, RBF 3 − , Ar—O − , wherein R comprises a substituent.

6. The complex of claim 5 , wherein R 2 , R 3 , R 4 , and R 5 comprise identical substituents.

7. The complex of claim 5 , wherein R 2 , R 3 , R 4 , and R 5 comprise tert-butyl groups.

8. The complex of claim 5 , wherein the poly-cyanostilbene macrocycle of Formula (IV) comprises:

Assignments (2)
CONFIRMATORY LICENSE Recorded Oct 23, 2017
From: INDIANA UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 044579/0529 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 20, 2017
From: FLOOD, AMAR H.; LEE, SEMIN; MCDONALD, KEVIN P.
To: INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION
Reel/Frame 043057/0758 →
Continuity (3)
Continuation In Part 14767570
Provisional Application 61764238 · Feb 13, 2013
Related Publication 20170313652A1 · Nov 2, 2017
Cited By (2)
US 12,320,774 US 12,692,272